Light emission from tryptophan oxidation by hypobromous acid

Luminescence

Volumn 28, Issue 6, 2013, Pages 853-859

  Petrônio, Maicon Segalla ^a   Ximenes, Valdecir Farias ^a  

^a SÃO PAULO STATE UNIVERSITY UNESP   (Brazil)

Author keywords

chemiluminescence; hypobromous acid; hypochlorous acid; taurine bromamine; taurine dibromamine; Tryptophan

Indexed keywords

AMINO ACIDS; BROMINE COMPOUNDS; CHEMILUMINESCENCE; CHLORINE COMPOUNDS; HORMONES; POLYCYCLIC AROMATIC HYDROCARBONS;

BROMAMINES; CELL-BE; CELL/B.E; HYPOBROMOUS ACID; HYPOCHLOROUS ACIDS; TAURINE BROMAMINE; TAURINE DIBROMAMINE; TRYPTOPHAN; TRYPTOPHAN OXIDATION; ULTRA-WEAK;

OXIDATION;

BROMATE; HYPOBROMOUS ACID; HYPOCHLOROUS ACID; TRYPTOPHAN;

ARTICLE; CHEMISTRY; CHEMOLUMINESCENCE; LIGHT; LUMINESCENCE; OXIDATION REDUCTION REACTION; SYNTHESIS; TAURINE BROMAMINE; TAURINE DIBROMAMINE;

CHEMILUMINESCENCE; HYPOBROMOUS ACID; HYPOCHLOROUS ACID; TAURINE BROMAMINE; TAURINE DIBROMAMINE; TRYPTOPHAN;

BROMATES; LIGHT; LUMINESCENT MEASUREMENTS; OXIDATION-REDUCTION; TRYPTOPHAN;

EID: 84890553540     PISSN: 15227235     EISSN: 15227243     Source Type: Journal    
DOI: 10.1002/bio.2445     Document Type: Article

References (29)

1. Widder EA,. Bioluminescence in the ocean: origins of biological, chemical, and ecological diversity. Science 2010; 328: 704-8.
2. Wijk Van RV, Van Wijk EP, Wiegant FA, Ives J,. Free radicals and low-level photon emission in human pathogenesis: state of the art. Indian J Exp Biol 2008; 46: 273-309.
3. Schwabl HH, Klima H,. Spontaneous ultraweak photon emission from biological systems and the endogenous light field. Forsch Komplementarmed Klass Naturheilkd 2005; 12: 84-9.
4. Xun S, Jingdong T, Zhaonan Z, Xinyuan L,. Chemiluminescence study on the peroxidation of linoleic acid initiated by the reaction of ferrous iron with hydrogen peroxide. Biophys Chem 1991; 40: 161-7.
5. Puntarulo S, Cederbaum AL,. Comparison of the ability of ferric complexes to catalyze microsomal chemiluminescence, lipid peroxidation, and hydroxyl radical generation. Arch Biochem Biophys 1988; 264: 482-91.
6. Zgliczyński JM, Olszowska E, Olszowski S, Stelmaszyńska T, Kwasnowska E,. A possible origin of chemiluminsecence in phagocytosing neutrophils. Myeloperoxidase-mediated chlorination of proteins and tryptophan. Int J Biochem 1985; 17: 393-7.
7. Watts BP Jr, Barnard M, Turrens JF,. Peroxynitrite-dependent chemiluminescence of amino acids, proteins, and intact cells. Arch Biochem Biophys 1995; 317: 324-30.
8. Baker N, Greenway GM, Wheatley RA, Wiles C,. A chemiluminescence nanosensor to monitor lipid peroxidation. Analyst 2007; 132: 104-6.
9. Vladimirov YA, Proskurnina EV,. Free radicals and cell chemiluminescence. Biochemistry (Mosc) 2009; 74: 1545-66.
10. Allen RC,. Environ. Role of oxygen in phagocyte microbicidal action. Health Perspect 1994; 102: 201-8.
11. Mayeno AN, Curran AJ, Roberts RL, Foote CS,. Eosinophils preferentially use bromide to generate halogenating agents. J Biol Chem 1989; 264: 5660-8.
12. Rees MD, McNiven TN, Davies MJ,. Degradation of extracellular matrix and its components by hypobromous acid. Biochem J 2007; 401: 587-96.
13. Thomson E, Brennan S, Senthilmohan R, Gangell CL, Chapman AL, Sly PD, et al,. Identifying peroxidases and their oxidants in the early pathology of cystic fibrosis. Free Radic Biol Med 2010; 49: 1354-60.
14. Schuller-Levis GB, Park E,. Taurine: new implications for an old amino acid. FEMS Microbiol Lett 2000; 226: 195-220.
15. Weiss SJ, Klein R, Slivka A, Wei M,. Chlorination of taurine by human neutrophils. Evidence for hypochlorous acid generation. Clin J Invest 1982; 70: 598-607.
16. Yazdanbakhsh M, Eckmann CM, Roos D,. Killing of schistosomula by taurine chloramine and taurine bromamine. Am J Trop Med Hyg 1987; 37: 106-10.
17. Marcinkiewicz J,. Taurine bromamine (TauBr) its role in immunity and new perspectives for clinical use. J Biomed Sci 2010; 17: Suppl 1:S3.
18. Ximenes VF, Fonseca LM, Almeida AC,. Taurine bromamine: a potent oxidant of tryptophan residues in albumin. Arch Biochem Biophys 2011; 507: 315-22.
19. Tokunaga S, Kanayama A, Miyamoto Y,. Modification of IkappaBalpha by taurine Bromamine inhibits tumor necrosis factor alpha-induced NF-kappaB activation. Inflamm Res 2007; 56: 479-86.
20. Thomas EL, Bozeman PM, Jefferson MM, King CC,. Oxidation of bromide by the human leukocyte enzymes myeloperoxidase and eosinophil peroxidase. Formation of bromamines. J Biol Chem 1995; 270: 2906-13.
21. Salminen H, Heinonen M,. Plant phenolics affect oxidation of tryptophan. J Agric Food Chem 2008; 56: 7472-81.
22. Stewart DJ, Napolitano MJ, Bakhmutova-Albert EV, Margerum DW,. Kinetics and mechanisms of chlorine dioxide oxidation of tryptophan. Inorg Chem 2008; 47: 1639-47.
23. Nguyen NT, Wrona MZ, Dryhurst G,. Electrochemical oxidation of tryptophan. J Electroanal Chem Interfac 1986; 199: 101-26.
24. Gottardi W, Nagl M,. Chemical properties of N-chlorotaurine sodium, a key compound in the human defence system. Arch Pharm (Weinheim) 2002; 335: 411-21.
25. Silva SO, Ximenes V F, Catalani LH, Campa A,. Myeloperoxidase-catalyzed oxidation of melatonin by activated neutrophils. Biochem Biophys Res Commun 2000; 279: 657-62.
26. Aspée A, Lissi EA,. Chemiluminescence associated with amino acid oxidation mediated by hypochlorous acid. Luminescence 2002; 17: 158-64.
27. Pollet E, Martinez A, Metha B, Watts BP, Turrens JF,. Role of tryptophan oxidation in peroxynitrite-dependent protein chemiluminescence. Arch Biochem Biophys 1998; 349: 74-8.
28. Alarcon E, Henriquez C, Aspee A, Lissi EA,. Chemiluminescence associated with singlet oxygen reactions with amino acids, peptides and proteins. Photochem Photobiol 2007; 83: 475-80.
29. Ximenes VF, Paino IMM, Faria-Oliveira de OMM, Fonseca da LM, Brunetti IL,. Indole ring oxidation by activated leukocytes prevents the production of hypochlorous acid. Braz J Med Biol Res 2005; 38: 1575-83.